186953-23-1

Upstream product

• 188263-82-3 1-((tert-butyldiphenylsilyl)oxy)-3-methyl-2-butene 
• 189437-81-8 (E)-4-(tert-butyldiphenylsilanyloxy)-2-methyl-but-2-en-1-ol 
• 556-82-1 3-methyl-2-buten-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 188263-80-1 tert-Butyl-diphenyl-((2E,4E)-(R)-3,7,11-trimethyl-dodeca-2,4,10-trienyloxy)-silane 
• 189438-06-0 (2E,6E)-1-(tert-Butyl-diphenyl-silanyloxy)-3,7,11-trimethyl-dodeca-2,6,10-trien-4-ol 
• 186953-24-2 ethyl (2E,4E)-6-[(tert-butyldiphenylsilyl)oxy]-2-fluoro-4-methylhexa-2,4-dienoate 
• 186953-33-3 (7E,9Z,13E)-tert-butyldiphenylsilyl 9-demethyl-9-fluororetinyl ether 
• 864971-49-3 ethyl (2Z,4E)-6-[(tert-butyldiphenylsilyl)oxy]-2-fluoro-4-methylhexa-2,4-dienoate 
• 874283-00-8 (R)-4-benzyl-3-[(2R,3R)-(E)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylhex-4-enoyl]-oxazolidin-2-one 
• 874283-15-5 (E)-(2R,3R)-6-(tert-butyldiphenylsiloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylhex-4-enal 
• 874283-14-4 (E)-(2R,3R)-6-(tert-butyldiphenylsiloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylhex-4-en-1-ol 
• 423118-80-3 (R)-4-benzyl-3-[(2R,3R)-(E)-6-(tert-butyldiphenylsiloxy)-3-methoxy-2,4-dimethylhex-4-enoyl]-oxazolidin-2-one 
• 874283-13-3 (R)-4-benzyl-3-[(2R,3R)-(E)-6-(tert-butyldiphenylsiloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylhex-4-enoyl]-oxazolidin-2-one 
• 874283-02-0 (E)-(2R,3R)-6-(tert-butyldiphenylsiloxy)-3-methoxy-2,4-dimethylhex-4-enal 
• 874283-01-9 (E)-(2S,3R)-6-(tert-butyldiphenylsiloxy)-3-methoxy-2,4-dimethylhex-4-en-1-ol 
• 423116-58-9 (1E,8E)-(5S,6S,7R)-10-(tert-butyldiphenylsiloxy)-5-hydroxy-1-iodo-7-methoxy-2,6,8-trimethyldeca-1,8-dien-3-one 
• 1013326-07-2 (E)-(2S)-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(Rs)-(toluene-4-sulfinyl)pent-3-en-2-ol 

Relevant academic research and scientific papers

An efficient total synthesis of (2E,4E,7R)-farnesa-2,4,10-triene from (R)-(+)-citronellal

(2E,4E,7R)-farnesa-2,4,10-triene(Caparratriene) (1), a novel sesquiterpene hydrocarbon with significant growth inhibitory activity against CEM leukemia cells, was first synthesized from (R)-(+)-citronellal (2) by employing titanium-induced intermolecular

Toward Leiodermatolide: Synthesis of the Core Structure

The macrocyclic core (35) of the marine natural product leiodermatolide (1) was synthesized from two key fragments, vinyl iodide 23 (C1-C11 part) and vinyl stannane 31 (C12-C18 part). A Stille coupling led to conjugated Z,Z-diene 32. The derived seco acid 34 was cyclized using a Yamaguchi macrolactonization. Key steps in the assembly of vinyl iodide 23 were a Paterson aldol reaction, and a Kumada coupling on a triflate derivative to create the C4-C5 trisubstituted double bond. The two stereocenters in fragment 31 were established by a Marshall-Tamaru reaction. The longest linear sequence comprises 20 steps.

The formal total synthesis of FR252921-An immunosuppressant

The formal total synthesis of FR252921 is described. The key steps include the preparation of three fragments starting from 1,4-butanediol, (R)-malic acid, and prenol, respectively, followed by two consecutive peptide couplings of the three fragments. Other key steps involve an allene-type rearrangement or enyne isomerization to install the triene moiety, a Seebach methylation, a Julia olefination to construct the trisubstituted diene unit, and an enzymatic resolution strategy to generate the C-18 stereocenter.

Total synthesis and biological evaluation of methylgerambullone

First total synthesis of methylgerambullone (MGB, 1) isolated from Glycosmis angustifolia was completed via a convergent route. The effect of MGB on the contractile responses of the isolated guinea-pig ileum induced by acetylcholine was investigated. As a result, it showed a potent relaxation rate (78.66 ± 4.30% at 100 mg/L) in a concentration-dependent manner on longitudinal smooth muscle contraction of isolated guinea-pig ileum induced by 1 μM acetylcholine.

Intramolecular Formal oxa-[3 + 3] Cycloaddition Approach to the ABD System of Phomactin A

(Equation Presented) The ABD-ring of phomactin A was synthesized using an intramolecular formal oxa-[3 + 3] cycloaddion of an α,β-unsaturated iminium salt tethered to a 1,3-diketone. This represents the first time that the 12-membered ring has been formed

Natural and unnatural terpenoid precursors of insect juvenile hormone

The biosynthesis of insect juvenile hormone (JH) is due, in part, to the precise head-to-tail coupling of allylic and homoallylic diphosphate substrates, as catalyzed by one or more prenyltransferases. To better understand this enzyme's role in JH production, homodimethylallyl diphosphate and both the natural and unnatural homologs of geranyl diphosphate have been prepared as potential substrates for insect prenyltransferase. These latter materials were constructed in a convergent manner by olefination of the corresponding trisnoraldehydes obtained from either terminal oxidative cleavage of geraniol or higher-order cuprate conjugate addition to acrolein. To aid in characterizing the nature of the terpenoid skeletons formed from our in vitro studies, homologous derivatives of farnesol were also prepared by anion coupling of the geranyl derivatives to either C5 or C6 allylic bromides. The preparation of these materials and the results of incubations with larval corpora allata homogenates of the lepidopteran Manduca sexta are described.

First total synthesis of (+)-caparratriene

Caparratriene (1), a new sesquiterpene hydrocarbon with significant growth inhibitory activity against CEM leukemia cells, was first synthesized starting from (R)-(+)-citronellal through 3 steps in an overall yield of 17.5%. The absolute configuration at